Polyalkylated 4-aminopiperidine derivatives

Abstract

New polyalkylated 4-aminopiperidine derivatives contain in their molecule two or three piperidine rings, each having two alkyl substituents at both the 2- and the 6- positions, optionally having substituents at the 1- and 3- positions and having an amino substituent at the 4- position. The piperidine rings are joined together by attachment of the 4-amino substituents through, where there are two piperidine rings, a polyalkylene, polyether or polyester chain, or through, where there are three piperidine rings, an isocyanurate or glycerol system. These compounds and their acid addition salts are useful as stabilizers for synthetic polymers.

We claim: 
     
       1. A compound of formula (I): ##STR383## wherein R 1  represents a hydrogen atom or a methyl group; R 2  represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, a cycloalkyl group having from 5 to 7 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from C 1  -C 4  alkyl and C 1  -C 4  alkoxy groups, a naphthyl group, an aralkyl group having 7 or 8 carbon atoms, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1  -C 4  alkyl and hydroxy groups, an alkylsulphonyl group having from 1 to 4 carbon atoms, a phenylsulphonyl group which is unsubstituted or has one or more C 1  -C 12  alkyl substituents, a group of formula --CONHR 3  wherein   R 3  represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a substituted phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl group or a cycloalkyl group having from 5 to 7 carbon atoms, or a group of formula --CH 2  CH 2  OZ;   when R 2  represents a hydrogen atom, Z of X and Y as defined herein below represents a hydrogen atom and when R 2  represents a group other than a hydrogen atom, Z represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an allyl group, a benzyl group, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1  -C 4  alkyl and hydroxy groups, or a group of formula --CONHR 9  wherein     R 9  represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl or a cycloalkyl group having from 5 to 7 carbon atoms; when R 2  represents a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms or a benzyl group, and, when R 2  represents a group other than a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms, a benzyl group, a 2,3-epoxypropyl group, an aliphatic acyl group having up to 18 carbon atoms or one of the groups of formulae ##STR384## wherein R 6  represents an alkyl group having from 1 to 4 carbon atoms;     R 7  represents a hydrogen atom, a methyl group or a phenyl group;   R 8  represents an alkyl group having from 1 to 18 carbon atoms; and   Z is as defined above; b represents 2 or 3; and   when b=2, X represents one of the groups of formulae ##STR385## m represents an integer of from 1 to 10; n represents an integer of from 1 to 10;     R 4  represents a hydrogen atom or a methyl group;   W represents one of the groups of formulae ##STR386## wherein p represents 0, 1 or 2;   R 5  represents a halogen atom;   q represents an integer of from 1 to 10; and   Z is as defined above; when b=3, X represents one of the groups of formulae ##STR387## wherein Z is as defined above, and an acid addition salt thereof.     
     
     
       2. A compound as claimed in claim 1, wherein R 1  represents a hydrogen atom. 
     
     
       3. A compound as claimed in claim 1, wherein R 2  represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, a cyclohexyl group, an alkanoyl group having from 2 to 12 carbon atoms, a benzoyl group or a group of formula --CH 2  CH 2  OZ' wherein Z' represents a hydrogen atom, an acetyl group or a benzoyl group. 
     
     
       4. A compound as claimed in claim 1, wherein X represents a group of formula ##STR388## wherein W' represents one of the groups of formulae ##STR389## --CO[CH 2  ] q  CO-- and --CH 2  CH 2  -- wherein q is an integer of from 1 to 10; Z' represents a hydrogen atom, an acetyl group or a benzoyl group, and n' is 0 or 1.   
     
     
       5. A compound as claimed in claim 4, wherein W' represents one of the groups of formulae ##STR390## n' represents 1. 
     
     
       6. A compound as claimed in claim 1, wherein Y represents a hydrogen atom, a methyl group, an allyl group or an acetyl group. 
     
     
       7. A compound as claimed in claim 1, wherein Z represents a hydrogen atom, an acetyl group or a benzoyl group. 
     
     
       8. A compound of formula (II): ##STR391## wherein R 12  represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms or a 2-hydroxyethyl group; X' represents a group of formula ##STR392## wherein W' represents one of the groups of formulae ##STR393## and --CH 2  CH 2  --, and n' represents 0 or 1; and   Y' represents a hydrogen atom or a methyl group.   
     
     
       9. A polymeric composition stabilized against photo- and thermal deterioration comprising a synthetic polymer and a stabilizing amount of stabilizer selected from the group consisting of compounds of formula (I): ##STR394## wherein R 1  represents a hydrogen atom or a methyl group; R 2  represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, a cycloalkyl group having from 5 to 7 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from C 1  -C 4  alkyl and C 1  -C 4  alkoxy groups, a naphthyl group, an aralkyl group having 7 or 8 carbon atoms, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1  -C 4  alkyl and hydroxy groups, an alkylsulphonyl group having from 1 to 4 carbon atoms, a phenylsulphonyl group which is unsubstituted or has one or more C 1  -C 12  alkyl substituents, a group of formula --CONHR 3  wherein   R 3  represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a substituted phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl group or a cycloalkyl group having from 5 to 7 carbon atoms, or a group of formula --CH 2  CH 2  OZ;   when R 2  represents a hydrogen atom, Z of X and Y as defined herein below represents a hydrogen atom and when R 2  represents a group other than a hydrogen atom, Z represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an allyl group, a benzyl group, an aliphatic, aromatic, araliphatic or alicyclic acyl group having up to 18 carbon atoms wherein the aryl moiety is unsubstituted or has one or more substituents selected from C 1  -C 4  alkyl and hydroxy groups, or a group of formula --CONHR 9  wherein     R 9  represents an alkyl group having from 1 to 18 carbon atoms, an unsubstituted phenyl group, a phenyl group having one or more substituents selected from methyl groups, chlorine atoms and bromine atoms, a naphthyl or a cycloalkyl group having from 5 to 7 carbon atoms; when R 2  represents a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms or a benzyl group, and, when R 2  represents a group other than a hydrogen atom, Y represents a hydrogen atom, an alkyl group having from 1 to 18 carbon atoms, an alkenyl group having 3 or 4 carbon atoms, a benzyl group, a 2,3-epoxypropyl group, an aliphatic acyl group having up to 18 carbon atoms or one of the groups of formulae ##STR395## wherein R 6  represents an alkyl group having from 1 to 4 carbon atoms;     R 7  represents a hydrogen atom, a methyl group or a phenyl group;   R 8  represents an alkyl group having from 1 to 18 carbon atoms; and   Z is as defined above; b represents 2 or 3; and   when b=2, X represents one of the groups of formulae ##STR396## m represents an integer of from 1 to 10; n represents an integer of from 1 to 10;     R 4  represents a hydrogen atom or a methyl group;   W represents one of the groups of formulae ##STR397## wherein p represents 0, 1 or 2;   R 5  represents a halogen atom;   q represents an integer of from 1 to 10; and   Z is as defined above; when b=3; X represents one of the groups of formulae ##STR398## wherein Z is as defined above, and acid addition salts thereof.     
     
     
       10. A composition as claimed in claim 9, wherein R 1  represents a hydrogen atom. 
     
     
       11. A composition as claimed in claim 9, wherein R 2  represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, a cyclohexyl group, an alkanoyl group having from 2 to 12 carbon atoms, a benzoyl group or a group of formula --CH 2  CH 2  OZ' wherein Z' represents a hydrogen atom, an acetyl group or a benzoyl group. 
     
     
       12. A composition as claimed in claim 9, wherein X represents a group of formula ##STR399## wherein W' represents one of the groups of formulae ##STR400## --CO[CH 2  ] q  CO-- and --CH 2  CH 2  -- wherein q is an integer of from 1 to 10; Z' represents a hydrogen atom, an acetyl group or a benzoyl group, and n' is 0 or 1.   
     
     
       13. A composition as claimed in claim 12, wherein W' represents one of the groups of formulae ##STR401## n' represents 1. 
     
     
       14. A composition as claimed in claim 9, wherein Y represents a hydrogen atom, a methyl group, an allyl group or an acetyl group. 
     
     
       15. A composition as claimed in claim 9, wherein Z represents a hydrogen atom, an acetyl group or a benzoyl group. 
     
     
       16. A composition as claimed in claim 9, wherein said stabilizer is selected from compounds of formula (II): ##STR402## wherein R 12  represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms or a 2-hydroxyethyl group; X' represents a group of formula ##STR403## wherein W' represents one of the groups of formulae ##STR404## and --CH 2  CH 2  --, and n' represents 0 or 1; and   Y' represents a hydrogen atom or a methyl group.